1. Field of the Invention
This invention pertains to phosphosulfonates, compositions containing these compounds and their use as herbicides.
The compounds of this invention provide control of many weed species, particularly grassy weeds. Although they may be used before or after the plant has emerged from the soil, they are especially effective when used to control growth of unwanted plants before the plants emerge from the soil.
Chemical weed control agents enable more efficient crop production by minimization of competing plant growth. New chemical means of controlling such unwanted vegetation are desirable to obtain better control of various agronomic weeds, for better crop safety and to overcome herbicide resistance.
The compounds of this invention control the growth of weeds while generally not injuring crops. The compounds primarily interfere with critical life processes in the germinating seed or seedling either causing plant death before growth above the soil or severely retarding growth of the plant so that the emerged shoot does not compete with the growing crop.
2. Description of Related Art
Czechoslovakian Patent CS 220,713 discloses dialkyl p-toluenesulfonyloxymethanephosphonates, specifically dimethyl and diethyl derivatives, as intermediates in the preparation of herbicides and insecticides. No information is provided as to any activity of the intermediates themselves.
Vizgert and Voloshin in Zhurnal Obshchei Khimii, Vol. 41, No. 9, pp 1991-4, disclose (dialkoxyphosphinyl)methyl arenesulfonates, including phenyl, 4-methylphenyl, 4-chlorophenyl and 3-nitrophenyl sulfonates. Vizgert et al. further disclose ethoxy, i-propoxy, n-propoxy, and n-butoxy as specific alkoxy substituents. No utility is suggested.
U.S. Pat. No. 4,456,464 relates to phenoxyphenoxyalkyl-, phenoxyphenylthioalkyl- and phenoxyphenylsulfonylalkyl-substituted phosphonates and phosphonites as herbicides.
U.S. Pat. No. 4,740,608 discloses (phosphomethyl)perfluoralkyl sulfonates as intermediates in the preparation of amino-phosphorous compounds, particularly N-phosphomethylglycine, a herbicide.
Chem. Abstracts 82: 72602p discloses [(dialkylphosphinyl)alkyl]arenesulfonates, (CH.sub.3 CH.sub.2 O).sub.2 P(O)CH(CH.sub.3)O.sub.3 SC.sub.6 H.sub.4 R, wherein R is hydrogen, 4-methylphenyl, 4-chlorophenyl and 3-nitrophenyl. No utility is disclosed.
Chem. Abstracts 83: 9009f discloses compounds of the formula CH.sub.3 OP(O)(R)CHR.sup.1 SO.sub.3 C.sub.6 H.sub.4 CH.sub.3 wherein R is phenyl or methyl and R.sup.1 is methyl or phenyl. No utility is disclosed.
Chem. Abstracts 83: 27382b discloses compounds of the formula RC.sub.6 H.sub.4 SO.sub.3 CH.sub.2 P(O)(OR.sup.1).sub.2 wherein R is hydrogen, 4-methyl, 4-chloro or 3-nitro and R.sup.1 is ethyl, isopropyl, butyl, 2-chloroethyl and pentyl. No utility is disclosed.
Chem. Abstracts 85:160247u discloses compounds of the formula C.sub.6 H.sub.4 SO.sub.3 CH.sub.2 P(O)(OR).sub.2 wherein R is hexyl or butyl which are intermediates in the synthesis of O-(dialkyloxyphosphinylmethyl)-phenylsulfonates.
Chem. Abstracts 88: 105477f discloses compounds of the formula R.sup.3 SO.sub.3 CH.sub.2 P(O)(OR.sup.2).sub.2 where R.sup.3 is phenyl or 4-methylphenyl and R.sup.2 is ethyl, propyl or isopropyl as starting materials in the synthesis of .alpha.-substituted methylphosphonates.
Chem. Abstracts 96: 85903b discloses the synthesis of dialkyl p-toluenesulfonyloxymethanephosphonates.
Chem. Abstracts 97: 163126n discloses compounds of the formula (phenoxy).sub.2 P(O)CH.sub.2 OSO.sub.2 C.sub.6 H.sub.4 R where R is 4-methyl, 4-chloro, 4-bromo and 3-nitro. No utility is disclosed for these compounds.
Chem. Abstracts 98:198639e discloses compounds of the formula 4-CH.sub.3 C.sub.6 H.sub.4 SO.sub.3 CH.sub.2 P(O)(OR.sup.2).sub.2 where R.sup.2 is methyl or ethyl as reagents in the process of making 5'-O-phosphonylmethyl analogs of nucleoside-5'-phosphates, 5'-diphosphates and 5'-triphosphates.